Cycle the Wine Regions of Tuscany
8 Days Starting and ending in Buonconvento, Italy
Visiting: Buonconvento, Murlo, Montalcino, Pienza, Bagno Vignoni, Montepulciano, Orcia Valley
Tour operator:
Tour code:
JTS
Group Type:
Independent
Guide Type:
Self Guided
Age range:
14-
Tour operated in:
EnglishTrip Styles:
Interests:
Activities:
Tour Overview
Embark on an unforgettable journey through the picturesque wine regions of Tuscany with our "Cycle the Wine Regions of Tuscany" tour. This self-guided adventure takes you through medieval villages, hilltop towns, and cypress-lined hills, offering breathtaking views and immersive experiences. Stay in a quintessential Tuscan estate and savor regional culinary specialties. Pedal through vibrant sunflower fields, olive groves, and vineyards, visiting historic sites like the 14th-century fortress in Montalcino and the stunning Sant’Anna in Camprena monastery. Enjoy relaxing rides to thermal waters in Bagno Vignoni and celebrate with a glass of Vino Nobile in Montepulciano. With hybrid bikes, digital navigation, and luggage transfers included, this tour ensures a seamless and enriching exploration of Southern Tuscany's unspoiled countryside.
Highlights
Itinerary
Day 1 : Arrive Buonconvento
Location: Buonconvento
Accommodation Name: Organic Farmhouse (Agriturismo)
Meals Included: Dinner
Make your own way to Buonconvento. For your 4 nights, you will be staying at an organic farmhouse (agriturismo) nestled amidst the magnificent rolling countryside of the Crete hills south of Siena. This large Tuscan estate produces olive oil, organic cereals and pasta that are used to prepare the typical regional dishes you will enjoy at their restaurant.
Day 2 : Circular Ride To Murlo & Le Befa (33Km/20.5Mi)
Location: Murlo
Accommodation Name: Organic Farmhouse (Agriturismo)
Meals Included: Breakfast, Dinner
A great first ride through the countryside on well kept dirt roads to Murlo. Immerse yourself in the dense woods as you ride by the Crevole River. Continue past steep cliffs to the sweet smell of bright yellow flowers and through an enchanting oak tree forest to La Befa. A short part of the trail is too narrow or rocky to cycle (about 300m) however the exhilarating views are more than worth the effort. Return to Buonconvento.
Day 3 : Circular Ride To Montalcino (24.1 Or 42.6Km/, 14.9 Or 26.4Mi)
Location: Montalcino
Accommodation Name: Organic Farmhouse (Agriturismo)
Meals Included: Breakfast, Dinner
Pedal through vibrant fields of sunflowers past Buonconvento to the heart of the Brunello wine district. The Monte Amiata volcano lures above as the surrounding countryside transforms into endless olive groves and vineyards. Ride steeply up to the fortified city of Montalcino where you can visit its magnificent 14th century fortress and Palazzo Comunale, then return to Buonconvento along remote back roads.
Day 4 : Cycle To Pienza (37.7Km/23.4Mi)
Location: Pienza
Accommodation Name: Hotel in Pienza
Meals Included: Breakfast, Dinner
Climb uphill to the renowned monastery of Monte Oliveto Maggiore with its delightful frescos and botanical garden. After replenishing your soul, follow a winding route past isolated villages until you reach a row of hundreds of cypress trees, inviting you to visit the stunning Sant’Anna in Camprena monastery. Admire the frescos then finish your day in the lovely town of Pienza.
Day 5 : Loop Cycle To Bagno Vignoni (27.7Km/17.2Mi)
Location: Bagno Vignoni
Accommodation Name: Hotel in Pienza
Meals Included: Breakfast, Dinner
Today is a relaxing day in which you will travel on smooth country roads to the medieval hamlet of Bagno Vignoni where you can rest and swim in its healing thermal waters, enjoyed by the Romans and home to the legendary water nymphs. Ride back to Pienza along gently undulating hills through unspoiled countryside embracing the essence of Southern Tuscany.
Day 6 : Circular Route To Montepulciano (34Km/21Mi)
Location: Montepulciano
Accommodation Name: Hotel in Pienza
Meals Included: Breakfast, Dinner
From Pienza, travel along immensely panoramic roads past the medieval stone-built hamlet of Monticchiello. Ride up a remarkable limestone ridge and enjoy breath-taking views of the Val d’Orcia. Gather your strength as you make the climb up to Montepulciano. Upon arrival, celebrate with a glass of the famous local Vino Nobile wine before freewheeling back to Pienza.
Day 7 : Cycle To Pieve A Slati Via Lucignano D'asso (24Km/15Mi)
Location: Orcia Valley
Accommodation Name: Organic Farmhouse (Agriturismo)
Meals Included: Breakfast, Dinner
The ride today is mostly on gravel road, gentle rolling hills in the most beautiful countryside of the Orcia valley. Half way you can stop in Lucignano d'Asso, a tiny village on the L'eroica cycle route. Then you ride back to the organic farm of Pieve a Salti where you spend your last evening.
Day 8 : Transfer To Buonconvento, Trip Concludes
Location: Buonconvento
Meals Included: Breakfast
After breakfast a short transfer takes you down to Buonconvento (arrange the time with the reception in advance), where you can catch the local bus or train to the airport for your onward journey.
What's Included
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Accommodation
4 nights 3 star agriturismo -
7 breakfasts
Enjoy 7 breakfasts during your stay.
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7 nights in 2-3 star hotels & agriturismo
Stay for 7 nights in 2-3 star hotels and agriturismo.
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Hybrid bike, pannier and odometer (1 per 2 bikes)
A hybrid bike, pannier, and odometer (1 per 2 bikes) are provided.
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Vehicle transfer day 8
Vehicle transfer is provided on day 8.
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Luggage transfer (1 bag per person not weighing anymore than 20kg)
Luggage transfer is included for 1 bag per person not weighing more than 20kg.
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Digital information pack: navigational App (can be used offline) with route notes & maps. Smartphone essential
A digital information pack with a navigational app (usable offline) including route notes and maps is provided. A smartphone is essential.
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Emergency hotline
Access to an emergency hotline is included.
What's Not Included
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Evening meals, all lunches & beverages
Evening meals, all lunches, and beverages are not included.
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Entrance fees
Entrance fees are not included.
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Travel insurance
Travel insurance is not included.
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Travel to the start and from the end point of the trip
Travel to the start and from the end point of the trip is not included.
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Personal expenses such as laundry and phone calls
Personal expenses such as laundry and phone calls are not included.
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Tourist taxes
Tourist taxes are not included.
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E-Bike, rear bags & odometer - must pre-book
E-Bike, rear bags, and odometer are not included and must be pre-booked.
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A supplement will apply if you are travelling solo or book a single room
A supplement will apply if you are traveling solo or book a single room.
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Guide - this is a self guided holiday
A guide is not included as this is a self-guided holiday.
Grading
Moderate trip on hilly terrain, very little shade on roads (Daily climb 350 to 750m). The rides follow mostly well asphalted country lanes and smooth turf roads (approx. 35% of the time) with very little traffic. More traffic near larger towns. *Please note that by Italian law, you can ride an electric bike if you’re 14 or over. For cyclists 14-18 years, wearing a helmet is compulsory.
Mode of Transport
Travel includes hybrid bike with pannier and odometer, vehicle transfer on day 8, and luggage transfer (1 bag per person not weighing more than 20kg).
Accommodation
Enjoy 7 nights in 2-3 star hotels and agriturismo, including stays at an organic farmhouse nestled amidst the rolling countryside of the Crete hills south of Siena.
Check out our Q&As
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What type of accommodation will we be staying in during the tour?
You will be staying in 2-3 star hotels and agriturismo, including an organic farmhouse nestled amidst the rolling countryside of the Crete hills south of Siena.
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What kind of bike will be provided for the tour?
A hybrid bike with pannier and odometer (1 per 2 bikes) will be provided. An E-Bike with rear bags and odometer is also available but must be pre-booked.
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Is this a guided tour?
No, this is a self-guided holiday. A digital information pack with a navigational app, route notes, and maps will be provided.
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What meals are included in the tour?
The tour includes 7 breakfasts. Evening meals, all lunches, and beverages are not included.
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What should I do if I encounter an emergency during the tour?
An emergency hotline is available for you to use during the tour.
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Are there any additional costs I should be aware of?
Yes, personal expenses such as laundry and phone calls, travel insurance, travel to the start and from the end point of the trip, and tourist taxes are not included. A supplement will apply if you are traveling solo or book a single room.
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What is the terrain like for cycling?
The trip is moderate on hilly terrain with very little shade on roads. The rides follow mostly well-asphalted country lanes and smooth turf roads (approximately 35% of the time) with very little traffic, although there is more traffic near larger towns.
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Are there any age restrictions for riding an electric bike?
By Italian law, you can ride an electric bike if you are 14 or over. For cyclists aged 14-18 years, wearing a helmet is compulsory.
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What happens on the last day of the tour?
After breakfast, a short transfer will take you down to Buonconvento, where you can catch the local bus or train to the airport for your onward journey.
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Self-guided holidays - inclusions
We have designed our self guided walking and cycling tours to include a number of elements to help you enjoy your holiday more, while leaving out some things to give you more freedom to tailor the trip to your needs and interests. Refer to the Trip Notes for more information on the specific inclusions for each trip. What’s included: - Detailed Route Notes - Accommodation - Luggage transfers - Any scheduled transfers as per Trip Notes - Emergency support - Some meals (mostly breakfasts) What’s NOT included: - Transport to/from start/finish points - Most meals - Any entrance/park fees - Travel insurance - Personal expenses along the way - Unscheduled transfers required during the trip
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Trip Grading & Preparation
Match your level of fitness & requirements Please read this information carefully to find out which grade is most suited to your level of fitness and requirements. To make the most of your Walkers' Britain holiday it is essential and your responsibility to choose a trip that is well within your capabilities. All our active holidays are graded and clearly marked in each trip description. All mountains have uphill and downhill sections and by definition walking and cycling demand some effort. However all things are relative, and these grades assume that you are a reasonably active person who enjoys walking or cycling. Few trips are extreme and most allow ample time for sightseeing and enjoying the scenery. If in doubt about the grade of any holiday, please contact us for advice or request the tour dossiers, you can also chat with our team about the right travel insurance for you. Grade 1 – Introductory These trips involve walking for four to five hours per day or cycling for 15-50 km per day at a slow but steady pace. You will need a reasonable level of fitness and good health. Suggested Preparation 30 minutes of aerobic-type exercise (either road cycling or jogging), three times a week for three months leading up to your trip. Grade 2 – Introductory to Moderate These trips involve a combination of what is described in our Introductory and Moderate levels. The emphasis is on introductory activity but including several moderate stages. Grade 3 – Moderate These adventures involve walking for up to six hours per day or cycling for up to 65 km per day, at a steady pace. You will need a good level of fitness and be in good health. Suggested Preparation 45 minutes of aerobic-type exercise (road cycling or jogging) three times a week for three months leading up to your trip. Grade 4 – Moderate to Challenging This trip grading involves a combination of what is described in our Moderate and Challenging levels. The emphasis is on moderate activity but including several challenging stages. Grade 5 – Challenging These active holidays involve walking up to nine hours per day in mountainous terrain with steep ascents and descents, pass crossing & alpine weather conditions, or cycling for up to 80 km per day over undulating terrain, with some steep and sustained hills. You will need an excellent level of fitness, be prepared to carry a daypack weighing up to 8 kg and be completely comfortable in adverse weather conditions. Suggested Preparation 1 hour of aerobic-type exercise five times a week for three to six months leading up to your trip. We also recommend regular hill walking with a pack in variable weather conditions or road cycling.
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Route notes
While our tours vary in terms of difficulty, route finding is made simple and convenient with our specially prepared package of maps and route notes. On many of the walks it is easy enough to navigate carefully using the route notes provided with a cursory glance at the map. As holidays reach the higher grades, you will need to take more care and we would expect you to have at least some knowledge of using a compass. Maps for our tours also vary considerably, from up-to-date GPS referenced additions, to old map copies which may still be the only ones obtainable for a particular area. The differences in style, grade and destinations of our tours are features that make them of continual interest and delight to our walkers & cyclists. Each set of route notes can contain the following elements relevant to the route: History and information on the region and the route you are walking. Detailed maps including points of interest and accommodation. Detailed step-by-step descriptions (with pictures) of the route and information on detours/optional additions. Transport timetables and information for getting there and away. Safety information and advice. Contact details of accommodation, transport, local representatives and emergency support. Advice for things to do along the way. Suggestions for dining and self catering.
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How our self-guided holidays work
Self guided walking and cycling holidays offer freedom, independence and choice, allowing you to tailor your holidays in the UK & Europe to your interest and travel style. Our detailed Route Notes will contain all of the information you need to plan how you would like to approach each day, giving you the freedom to set your own pace. As you are not limited by the constraints of group travel, you are free to shorten or lengthen your walk as the terrain permits and can even take a day off, although you may need to travel onto your next accommodation by taxi or public transport in order to do so.
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Oct 31, 2025 - Nov 07, 2025Book with Confidence
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Low Deposit
Walkers' Britain requires a minimum deposit of 250 GBP per person or the full booking value, whichever is less, with the final balance not due until 70 days before departure.
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Cancellation Policy
We don't charge a cancellation fee, here is a summary of walkers' britain charges.
Up to 70 days before tour starts: Forfeit 100% of deposit.
At 69 days before tour starts: Forfeit 50% of booking price.
At 35 days before tour starts: Forfeit 100% of booking price.